"We want to find a good idea that looks like it's a bad idea," Horowitz said, recounting how he was turned onto Airbnb. "If it looks like a good idea, it’s not innovative enough, because other people can see it. Apple and Samsung can see it. And they've got way more money and they're going to compete you out of the market."

In some cases, he said, getting an Andreessen Horowitz investment can actually be bad for startups — too many folks will spot it and try to compete.

"At that point, we had nothing to lose. Leaders had to think big," he said. "It would become a moment when we began to transform Chicago."

Fast forward to 2016, when more than 180 Chicago tech companies raised more than $1.7 billion and when 55 companies had exits totaling another $1.7 billion, he said. All the successes make Chicago distinct, he said — and not needing to mimic Silicon Valley.

"I do not want to be silicon anything," Pritzker said. "We are trying to build something unique here."

When Chicago’s startups haven’t worked out, it’s still been a boon for the city’s heavyweights like Grubhub, said Matt Maloney.

It's a result of the growth of the startup ecosystem getting to the point where so many entrepreneurs are taking chances, he said in a closing keynote with ChicagoNext chairman Mark Tebbe ⇒.

"We've had some great hires picking through the remnants of startups that didn't work," he said. "When I was building, I was pulling people out of banks … and it was really hard.”

Maloney has already mapped out his Plan B in case things go south with Grubhub: He's a fan of restaurant-booking startup Tock.

"If I got fired, I'd ask them for a job," he said.

Outsiders or insiders?

Many of the tech leaders, venture capitalists, corporate VCs and angel investors checking out the emerging tech companies for funding opportunities appear familiar with each other. About 70 percent of the 450 attendees are from the Chicago area, organizers said.

About 125 people were at the 1871 program Wednesday for tours and presentations and heard from startups connected with Techstars Chicago, the Impact Engine investment fund and the BMO Harris-sponsored FinTech program.

Much of the action was in the hallway outside of sessions. Speakers were often hemmed up by hives of people for 30 minutes straight. Karen Kerr from GE Ventures was pretty popular in one corner after appearing on a panel about industries of the future: After one group chatted her up, then a man from a security startup approached her, followed by an mHub executive.

And inside the auditorium where the panels and presentations take place, almost every panel has had a shout-out to 1871, sometimes multiple times per session.

Jeff Rinvelt, from Renaissance Venture Capital Fund in Ann Arbor, Mich., said these meetings are important for the prospecting new investments.

"In the public market space, everybody has the same information. Little bits of information can mean a lot to your investment strategy and the way you invest. You're looking here for little bits of information that you can use to make big moves in your company," he said during a reception at TechNexus. "We come to these knowing that 90 percent of the time it's useless. But the 10 percent is why we keep going."

Patricia Glaza, vice president at Invest Detroit Ventures, said she appreciates the opportunity to meet with other investors.

"We're connecting with accelerator programs and the other venture firms we can share deals with or pass along as our companies mature and pass them along," she said. "It's building relationships. The stronger you have relationships, the easier it is to dialogue."

She was a fan of the rapid-fire pitches on the first day.

"We're a broad investor in lots of different industries. It gives me a chance to connect and interact with lots of different groups throughout the day," she said. "It's always interesting to see what's happening in different parts of Chicago. Seeing all the different startups and coworking spaces and accelerators and programs that were available is almost like a mini city tour."

Minal Shankar, a senior investment associate at a San Francisco venture capital firm, said her firm hasn't traditionally looked much in the Midwest.

"It's great to see Chicago has a very healthy and flourishing venture ecosystem and startup ecosystem. For us, getting those 30-second snippets of as many companies as possible gives you a lot of data points really quickly to be able to see what fits our criteria."